test_final_spring_05 - A. Nomenclature: (15 points) ' '...

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Unformatted text preview: A. Nomenclature: (15 points) ' ' Give an acceptable IUPAC name for each of the following compounds. Be sure to lndlcate the ‘ stereochemistry where appropriate. B. Facts: 8 points 1. Place the ietter of the more stabie resonance contributor in the box. (2 pts.) H H 0’ +0” A A D A B C. Reactions: Totai = 32 points, 8 points each Please provide the reagents or major product in the answer box. Be sure your drawing indicates stereochemistry if applicable. Partiai credit is awarded only when intermediate products in a multi—step reaction are shown beiow the reaction. ' 1. CH3NH2/ NaBHSQN 1_ O 2. CH3] (XS) | —----“—_—"""" 3. A920 IHQOlheat 4. MCPBA 5. CH3O’ Na+l CH3OH 5. H30+ Note: MCPBA = m—chloroperbenzoic acid a 1. Big {CH3COZH 2. . \ o 2. I f " A/ N 3. or (CH3)3CO'Na+ 00H3 4' (gram—Q NH2 OCH3 NH2 No2 4,0 — CHZCHa OCHa Br D. Mechanism: (15 points) Provide a clear mechanism to explain the formation of the product. use curved arrows to indicate "electron. flow". a -n-u-- - n- . - u ‘ =e . v u - Show allintermedlates and all formal charges. When more than one resonance contributor may be drawn, be sure to draw the most stable contributor. ' O o H W + “NOE NaOEt I EtOH. O ogN Cl E. Synthesis: 15 Points Synthesize the molecule belpw using any of the following reagents'ibenzene, cyclohgggane, amt three carbons or less,” any Inorganic reagents, any oxidizing or reducmg agents, and any‘peroxyaCIds. CH3 0 0 ll II CLO-CIMCHECHTC ("3-OCHon3 ' o F. Spectroscopy: 15 Points A compound with‘the formula C4H11N exhibits the IRJH NMR and proton decoupled 13C) NMR spectra shown below. Please identify this compound and draw the structure in the box provnded below. 2 TRHMTTHGC‘E :Ipil [Ir-g m- hatuun salt les W mwific 1992 3H 3H IH 3.5 3.0 2.5 2.0 1.5 1.0 PPM 0.5 PmImNMR 5.45 111.43 11.“: :5. 17.49 D TABLE 13.3 Approximate proton chemical shifts TYPE OF PROTON CHEMICAL SiliFT (5. ppm} 1" Alkyl. llClI, (LB— LEI 2° Aim. RCH,R 1.2— 1.4 3° Allzyl, M21: l.4—l.7 Allylic. R2C=C-C'H, l.6—1.9 Ill . Kelmp. RCCI-l;1 2.1.4.5 D Banzyllc. AICH, 2.2-4.5 Acclylcnlc. REE-CH 2.5-4.1 Aikyl iodidc. RCH-fl 3.1—3.3 mm. ROCHIR 3.3—3.9 Alcnhul. HOCH2R 3.3—4.0 Alkyl bromide, RCIl-flir 3.4 —3.6 AIkYI-chloridc, RCH=CI 3.6—3.8 Vinynic. mam-zen, 4164.0 Vinylic, R1C=CH 5.2—5.7 l Aromatic. Al'H 6.0—9.5 Aldcllyllc, Rfili 9.5—9.6 0 Alcohol laydroxyi. ROB 0.5—6.0“ Amino, R—N'll; 1.0—5.0'l Phanulic, AID“ 4.5—7.1; CnflmxyliLl. Rcfllflll Ill—13' O . ._.—.._...,..._a.._--————-v—- " 11M: cllzmlcnl shifls of thus: prawns vary in dlfiuranl mlvenls and wilh lempcrnlur: Ind comcmnliun. TABLE 13.4 Approxlmate carbon-13 chemical shifts .——-u——-l——“‘_'———--—'——W-fl‘_-—rm ------ —-v TYPE OF cannon ATOM CHEMlcm. mm «a. ppml ‘_-__.__,.,—___n.-—-—""—‘———""-'—'—-.___ ____ ._.._ _ l°AlkyL RCH, - ' r ' 7 0—40 2“ Alkyl, RCH2R [fl-SI] 3° A1kyl.RCHR-_. _ . ' - 15411 1 ~ I ; Alkyl lmllde or amine, —$—X X - Cl, Br. or N— Ill—(15 Alcohol nr elhcr, —JI3—‘D 50—90 Alkync, —-C—=— fill—90 Allan; \lCfi lllll- I'Il'l I m1_(O — Hun—I'm Nilrilns. —CEN 120-- LED 0 ll 1 Amides. —C"—N— I50— | $0 (“I ll thnxylic acids. csnzrs, “FL—0 160— HIS 0 ll Aldelwtlus, kcmnes.«-C- lfilnllfi FREQUENCY GROUP RANGE 1:11.": U?!"— '"""" an. _rH____h~—________._...____———~—--+— A. Allin C—H (sunlnlfiugj lsopmpyl,----Cl'I{(.'.‘I-.l1)a 2853 — 2961 1380- [385 and 1365— 1370 1385—1395 tart—EULVL —C(CH:|)3 - and ~ 1365 B. Alltenyl C—H (sunning) 3m 0—3095 C=C (stretching) 1620—1680 R—CH=CH, 985—1000 and 905-— 920 R;.C==C‘l'lz (out-of-plane 880—900 m.RCH=CHR _ C —H “Ming” 515—730 Imus-RCH—CHR 950—- 975 C. Alicny EC-H (snatching) " -— 3300 CEC (stretching) 2100—2260 1). Aromatic V AI—H' (mucking) - - 3030 Amrnnfic submituticn type (C—H oul-af-plu: handings) Monosubslimln'd 690—710 and 730-770 a Disnbstitmed 735—170 . m Disubstimlnd 680—725 . and 750—810 1:- Disubsdlmad BOD—840 r. Alcohols, W5. and Cnrbuxylic Acids . 0-H (mulching) Alcohols, phenols (dilute solutions) 3590-3650 Alcohols. phnnols (hydrogen bonded) 3200—3550 Carbozyfic acids (hydrngzn bonded) 2500—3000 5. Aldehydes. Kaummfmem and. Carboxyliv; Acids C=O (stretching) 15304780 Aldehydai 1690—1740 Humans _ 7 1680—1750 Ems ‘ 1735 — 1750 Carbnzylic abids 171011780 Amidcs . 15304690 G. Amines N—H 3300-3500 H. Nitrils ‘CEN 2220—1260 (111—51 (5) [5) (m) (s) (m) (5) (s) (s) (s) {s} (V) {vary 5) (very S) {s} (5) (very 5) (vary 3) (sharp. V) (brand. 3) (broad. v] (s) (s) (s) (s) (5) km) (ml ‘HF,__.—._......__————-—-u-—-—--— ' Abbmuinuaus: s I umng. m - Indium, w - wank. v :- vafiahlz. -— u nppmximamly. ...
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This note was uploaded on 01/05/2012 for the course CHEM 3321 taught by Professor Bean during the Spring '11 term at American Jewish University.

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test_final_spring_05 - A. Nomenclature: (15 points) ' '...

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